I converted about 100 cassette tapes to digital files and then saved them to CDs a few years ago. I needed to have a cassette deck with an audio out jack which I didn't have, so I borrowed one. The software I used was Spin It Again. It was very easy to use and allowed you to removed tape hiss and other noise. You could also separate the songs and download the Album art too.

I'm sure there are other options out there too that someone else has used.

It was an audio out - white and red (two cables) - to 3.5 mm (one cable) which plugs into the back of your computer's sound card input. If you don't have one, don't buy it... I'll get you mine. It's only good for one thing and I'm done using it.

Yes, those are like the ones I have. It has two RCA (white and red) jacks for the cassette player deck and an audio jack for the sound card on your computer. You plug it in to the sound "in" on the sound card. But I don't think you can use a headphone jack "out" from the tape deck player to go to the sound card on your computer. I'm not sure though. I still have the old tape deck I used if you need one with RCA jacks for the audio out.

An audio out to your soundcard including the headphone connector will work. You only need a cable that fits into headphone on one end and sound card on other.

As for a recording program here is the most amazing recording tool I've ever seen. You can download a free trial to used it. Use is limited but reinstalling program allows you to "Test it again"

I bought the thing ten years ago 32 bit and when buying a 64 bit system they gave me a free upgrade. Upgrades are free for lifetime.

I recorded a 1960's LP into the program. The filtering properties are so good at removing pops, tics, hum and hiss the resulting CD sounded like a brand new digital recording. It cost about 50$ but if you like to play with

audio this program is top shelf.

You can also add ambiance making your recording sound "Live" "Studio" etc there are hundreds of options. You can even record backwards. Check it out. After ten years I would not be without this thing well worth the money.

I've recorded hundreds of old albums and tapes with unbelievable results.